4-Methylmorpholine → 1,1-Dimethylethyl 4-[[2-(4-chlorophenyl)acetyl]amino]-1-piperidinecarboxylate

HRID 242645노트

반응식

HRID 242645 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23](O)=[O:24])=[CH:18][CH:17]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:23](=[O:24])[CH2:22][C:19]2[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 5

HCID 79724-MethylmorpholineHCID 15880(4-Chlorophenyl)acetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 12682914-Amino-1-Boc-piperidine

생성물 1

HCID 470691701,1-Dimethylethyl 4-[[2-(4-chlorophenyl)acetyl]amino]-1-piperidinecarboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-amino-piperidine 1-carboxylic acid tert-butyl ester (0.44 g, 2.2 mmol) and 4-chlorophenyl acetic acid (0.34 g, 2 mmol) in dichloromethane (10 mL) were added EDCI (0.55 g, 2.8 mmol), HOBT (0.42 g, 2.8 mmol) and N-methylmorpholine (0.6 g, 6 mmol) and the resulting mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo, diluted with dichloromethane and extracted with saturated aqueous sodium bicarbonate solution. The aqueous layer was back extracted twice with dichloromethane. The combined organics were dried over sodium sulfate and concentrated in vacuo. Crude product was purified using a short plug of silica gel using ethyl acetate to give the desired product 1H-NMR (CDCL3) δ: 1.15-1.25 (2H, m), 1.40 (9H, s), 1.80-1.90 (2H, m), 2.85 (2H, dd), 3.5 (2H, s), 4.00 (1H, br s), 5.20 (1H, d), 7.15-7.35 (4H, m). ESI-MS m/z: 353 (M+1), UV retention time: 2.47 min.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with dichloromethane
  3. extractionextracted with saturated aqueous sodium bicarbonate solution
  4. extractionThe aqueous layer was back extracted twice with dichloromethane
  5. dry with materialThe combined organics were dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customCrude product was purified

출처 및 근거

ORD 기록
ord-b486d7a15bf746ca8de6cab25e111a31
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653096B2

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